how is kanamycin produced

Full Answer

What is the history of kanamycin?

Kanamycin was first isolated in 1957 by Hamao Umezawa from the bacterium Streptomyces kanamyceticus. It was removed from the World Health Organization's List of Essential Medicines in 2019.

How do you make a kanamycin solution?

Preparation Step 1: To prepare 10 ml of stock solution of kanamycin, weigh out 500 mg of kanamycin. Transfer it to a 15 ml screw-capped tube. Add 9 ml of deionized / Milli-Q water. Mix until all kanamycin is completely dissolved. Tip: We recommend using a 15 ml screw-capped tube with milliliter marks.

What is the composition of kanamycin?

Kanamycin is an aminoglycoside antibiotic, which is a mixture of three chemicals: kanamycin A, B, and C, in which kanamycin A is the main component. Kanamycin was isolated from the bacterium Streptomyces kanamyceticus by Hamao Umezawa in 1957 [51].

How does kanamycin work?

Veterinary Drug -> GROWTH_PROMOTER; Kanamycin is an aminoglycoside antibiotic. Aminoglycosides work by binding to the bacterial 30S ribosomal subunit, causing misreading of t-RNA, leaving the bacterium unable to synthesize proteins vital to its growth.

How is kanamycin made?

Kanamycin is isolated from the bacterium Streptomyces kanamyceticus and its most commonly used form is kanamycin sulfate.

What is the purpose of kanamycin?

Kanamycin injection is used to treat serious bacterial infections in many different parts of the body. This medicine is for short-term use only (usually 7 to 10 days). Kanamycin belongs to the class of medicines known as aminoglycoside antibiotics. It works by killing bacteria or preventing their growth.

What is kanamycin in biology?

Kanamycin (Kanamycin A) is an antibiotic compound isolated from the bacterium Streptomyces kanamyceticus. It belongs to the aminoglycoside class of antibiotics and is mainly effective against Gram-negative bacteria.

Is kanamycin the same as ampicillin?

The inhibition blocks the binary fission and leads to cell lysis, ampicillin is a BACTERICIDAL agent. On the other side kanamycin inhibits the protein synthesis by blocking the 30s subunit of the ribosome. Kanamycin acts as an BACTERISTATIC agent it arrests the growth and proliferation of cells.

What type of antibiotic is kanamycin?

Kanamycin belongs to the class of medicines known as aminoglycoside antibiotics. It works by killing bacteria or preventing their growth. However, this medicine will not work for colds, flu, or other virus infections.

What is the generic name for kanamycin?

Kantrex (kanamycin) Injection is an aminoglycoside antibiotic used to treat serious infections caused by bacteria.

What bacteria is kanamycin resistant?

In Escherichia coli, mutations at positions 1408, 1409, and 1491 (equivalent to positions 1400, 1401, and 1483 of M. tuberculosis, respectively) caused resistance to kanamycin, paromomycin, and other aminoglycoside antibiotics (9, 20).

What is the mechanism of action of kanamycin?

Kanamycin is an aminoglycoside antibiotic used to treat different types of bacterial infections. Kanamycin works by binding to the bacterial 30S ribosomal subunit, causing misreading of mRNA and leaving the bacterium unable to synthesize proteins vital to its growth.

Which kanamycin is more active and why?

Tobramycin is 3'-deoxykanamycin B (Figure 3). This one change renders it more potent than the kanamycins against Gram-negative bacteria, including certain resistant strains.

Is E. coli resistant to kanamycin?

Kanamycin, an aminoglycoside antibiotic, can inhibit the peptide synthesis of E. coli by blocking the translocation process (Semenkov et al. 1982).

Is tetracycline and kanamycin same?

Kanamycin interacts with the 30S ribosomal subunit resulting in a significant amount of mistranslation and prevents translocation during protein synthesis [27, 28], whereas tetracyclines bind to the 16S part of the 30S ribosomal subunit and prevent amino-acyl tRNA to attach at A-site of mRNA-ribosome complex, ...

Is kanamycin an antifungal?

A simple structural modification turns the clinically obsolete antibacterial kanamycin into an antifungal agent. Structure–activity relationship studies have led to the production of K20, an antifungal kanamycin that can be mass-produced for uses in agriculture as well as in animals.

What bacteria is kanamycin effective against?

Kanamycin A is similar to streptomycin and neomycines, and it possesses a broad spectrum of antimicrobial action. It is active with respect to most Gram-positive and Gram-negative microorganisms (staphylococci, colon bacillus, klebisella, Fridlender's bacillus, proteus, shigella, salmonella).

What is the mechanism of action of kanamycin?

Kanamycin is an aminoglycoside antibiotic used to treat different types of bacterial infections. Kanamycin works by binding to the bacterial 30S ribosomal subunit, causing misreading of mRNA and leaving the bacterium unable to synthesize proteins vital to its growth.

What does kanamycin do to E coli?

Kanamycin, an aminoglycoside antibiotic, can inhibit the peptide synthesis of E. coli by blocking the translocation process (Semenkov et al. 1982). In this work, green fluorescent protein was selected as a reporter, and kanamycin was selected as a representative for antibiotics.

What bacteria is kanamycin resistant?

In Escherichia coli, mutations at positions 1408, 1409, and 1491 (equivalent to positions 1400, 1401, and 1483 of M. tuberculosis, respectively) caused resistance to kanamycin, paromomycin, and other aminoglycoside antibiotics (9, 20).

Which kanamycin is converted to kanamycin A?

One of the branches forms kanamycin C and kanamycin B, while the other branch forms kanamycin D and kanamycin X. However, both kanamycin B and kanamycin D can be converted to kanamycin A, so both branches of the pathway converge at kanamycin A.

How does kanamycin work?

Kanamycin works by interfering with protein synthesis. It binds to the 30S subunit of the bacterial ribosome. This results in incorrect alignment with the mRNA and eventually leads to a misread that causes the wrong amino acid to be placed into the peptide. This leads to nonfunctional peptide chains.

What is the main product of Streptomyces kanamyceticus?

Biosynthesis. While the main product produced by Streptomyces kanamyceticus is kanamycin A, additional products are also produced, including kanamycin B, kanamycin C, kanamycin D and kanamycin X. The kanamycin biosynthetic pathway can be divided into two parts.

How long does kanamycin last?

It is used by mouth, injection into a vein, or injection into a muscle. Kanamycin is recommended for short-term use only, usually from 7 to 10 days. As with most antibiotics, it is ineffective in viral infections. Common side effects include hearing and balance problems. Kidney problems may also occur.

What is kanamycin used for?

Kanamycin A. Kanamycin A, often referred to simply as kanamycin, is an antibiotic used to treat severe bacterial infections and tuberculosis. It is not a first line treatment. It is used by mouth, injection into a vein, or injection into a muscle.

Why does the Kanamycin pathway split into two branches?

At this point the kanamycin pathway splits into two branches due to the promiscuity of the next enzyme, which can utilize two different glycosyl donors - UDP-N-acetyl-α- D -glucosamine and UDP-α- D -glucose. One of the branches forms kanamycin C and kanamycin B, while the other branch forms kanamycin D and kanamycin X.

What is the first part of an antibiotic?

The first part is common to several aminoglycoside antibiotics, such as butirosin and neomycin. In it a unique aminocyclitol, 2-deoxystreptamine, is biosynthesized from D -glucopyranose 6-phosphate in four steps.

What is kanamycin injection?

Kanamycin injection is indicated in the short-term treatment of serious infections caused by susceptible strains of the designated microorganisms below. Bacteriological studies to identify the causative organisms and to determine their susceptibility to Kanamycin should be performed. Therapy may be instituted prior to obtaining the results of susceptibility testing.

How long does it take for kanamycin to be absorbed?

The drug is rapidly absorbed after intramuscular injection and peak serum levels are generally reached within approximately one hour. Doses of 7.5 mg/kg give mean peak levels of 22 mcg/mL. At 8 hours following a 7.5 mg/kg dose, mean serum levels are 3.2 mcg/mL. The serum half-life is 2 1/2 hours. Intravenous administration of Kanamycin over a period of one hour resulted in serum concentrations similar to those obtained by intramuscular administration.

Why is it important to monitor renal function with kanamycin?

Because of high concentrations of Kanamycin in the urinary excretory system, patients should be well hydrated before treatment to prevent irritation of the renal tubules.

What nerves does Kanamycin affect?

As with other aminoglycosides, the major toxic effects of Kanamycin are its action on the auditory and vestibular branches of the eighth nerve and the renal tubules. Neurotoxicity is manifested by bilateral auditory toxicity which often is permanent and, sometimes, by vestibular ototoxicity. Loss of high frequency perception usually occurs ...

How long does kanamycin stay in your system?

The serum half-life is 2 1/2 hours. Intravenous administration of Kanamycin over a period of one hour resulted in serum concentrations similar to those obtained by intramuscular administration. Kanamycin diffuses rapidly into most body fluids including synovial and peritoneal fluids and bile.

What is the best way to remove kanamycin from the blood?

In the event of overdosage or toxic reaction, hemodialysis or peritoneal dialysis will aid in the removal of Kanamycin from the blood. In the newborn infant, exchange transfusion may also be considered.

Why is kanamycin used in medicine?

To reduce the development of drug-resistant bacteria and maintain the effectiveness of Kanamycin Injection and other antibacterial drugs, Kanamycin Injection should be used only to treat or prevent infections that are proven or strongly suspected to be caused by susceptible bacteria. When culture and susceptibility information are available, they should be considered in selecting or modifying antibacterial therapy. In the absence of such data, local epidemiology and susceptibility patterns may contribute to the empiric selection of therapy.

What is the amino group of kanamycin?

1 ). Because the 6-amino-6-deoxy- d -glucose moiety of kanamycin A is largely derived from d -glucosamine, rather than d -glucose, 140 the amino group at the C2 of glucosamine or neosamine C (2,6-diamino-2,6-dideoxy- d -glucose) appears to be deaminated in the late stages of the biosynthesis. In the kanamycin biosynthetic gene cluster, two unique enzymes, the α-ketoglutarate-dependent non-heme iron dioxygenase KanJ and the NADPH-dependent reductase KanK, are encoded. 141 KanJ recognizes kanamycin B and catalyzes the hydroxylation at the C2′ to afford a hemiaminal intermediate, which is then transformed to the 2′-oxointermediate by releasing ammonia ( Fig. 19 ). The 2′-oxointermediate is then reduced by KanK stereoselectively to afford kanamycin A. A kanJ gene-inactivated mutant accumulated kanamycin B, which indicates that the modification reaction of the neosamine C moiety in kanamycin B by KanJ is crucial for kanamycin A biosynthesis. 142,143 It has also been reported that the introduction of kanJ and kanK genes into a gentamicin producer strain resulted in the formation of deaminated 2′-OH-containing gentamicins. 100,144

What is the difference between kanamycin and kanamycin B?

Kanamycin A, produced by S. kanamyceticus, was the first member of this family, while kanamycin B differs in having a 4-O-diaminosugar on 2-DOS ( Figure 3 ). 22–24 This single change makes the latter approximately twice as active in vitro. 4 Both kanamycins exhibit a broad spectrum of activity and have been important commercial antibiotics in many countries. 2

How do aminoglycosides affect bacteria?

Aminoglycosides manifest their bactericidal activity by binding to the bacterial 30S ribosomal subunit. This binding interferes with the initiation of protein synthesis by fixing the 30S–50S ribosomal complex at the start codon of mRNA ( Chambers 2006; Mingeot-Leclercq et al. 1999 ). The formation of the 30S–50S ribosomal complex has a variety of effects deleterious to bacteria. These include obstructing further translation, misreading mRNA leading to premature termination, and incorporating incorrect amino acids resulting in abnormal or nonfunctional proteins ( Clark and Chang 1965; Davies et al. 1965; Kuhberger et al. 1979; Tai and Davis 1979; Weisblum and Davies 1968 ). These abnormal and nonfunctional proteins may then be incorporated into the cell membrane compromising membrane integrity. In addition, the abnormal proteins may alter cell membrane permeability and increase aminoglycoside transport into the cell.

Is amikacin a kanamycin?

Amikacin is a semisynthetic aminoglycoside antibiotic. It is derived from kanamycin A by acetylation with an S-4-amino-2-hydroxybutyryl (AHB) side chain at the 1-position of its deoxystreptamine moiety. Amikacin shares many physical, chemical, pharmacologic, and toxicologic properties with kanamycin. However, it has a broader antibacterial spectrum than kanamycin, gentamicin, and tobramycin. The AHB side chain accounts for the stability of amikacin towards most bacterial plasmid-mediated enzymes responsible for resistance to the aminoglycosides. As a result, amikacin is active against many gentamicin- and tobramycin-resistant gram-negative bacilli …

Is kanamycin a neomycin?

Kanamycin A is similar to streptomycin and neomycines, and it possesses a broad spectrum of antimicrobial action. It is active with respect to most Gram-positive and Gram-negative microorganisms (staphylococci, colon bacillus, klebisella, Fridlender’s bacillus, proteus, shigella, salmonella).

Does kanamycin inhibit splicing?

Kanamycin A did not inhibit splicing and had no effect on the pattern of chemical modification of RNA. From: Reference Module in Chemistry, Molecular Sciences and Chemical Engineering, 2013. Download as PDF. About this page.

Is amikacin a gram negative drug?

Amikacin incorporates an additional (S)-4-amino-2-hydroxybutyl (AHB) side chain into the 1-amino position of the deoxystreptamine moiety of kanamycin A, resulting in increased stability against most of the bacterial plasmid-mediated enzymes, which are responsible for resistance to aminoglycosides [25]. Because of this, amikacin is active against many gentamicin- and tobramycin-resistant gram-negative bacteria [25]. A dose of 15–20 mg/kg is recommended both as a once-daily dose or in two divided doses [25]. To avoid toxicity, trough concentrations of <5 mg/L have been proposed [2].

What is kanamycin used for?

Kanamycin (also known as kanamycin A) is an aminoglycoside bacteriocidal antibiotic, available in oral, intravenous, and intramuscular forms, and used to treat a wide variety of infections. Kanamycin is isolated from the bacterium Streptomyces kanamyceticus and its most commonly used form is kanamycin sulfate.

How long does kanamycin last?

In premature infants, the elimination half-life of kanamycin reportedly averages 9 hours. In patients with severe burns, plasma half-life and plasma concentrations of the drug may be decreased. Plasma concentrations are higher and the elimination half-life of kanamycin is prolonged in patients with renal impairment.

What is the concomitant and/or sequential use of aminoglycosides?

Concomitant and/or sequential use of an aminoglycoside and other systemic, oral, or topical drugs that have neurotoxic, ototoxic, or nephrotoxic effects (e.g., other aminoglycosides, acyclovir, amphotericin B, bacitracin, capreomycin, certain cephalosporins, colistin, cisplatin, methoxyflurane, polymyxin B, vancomycin) may result in additive toxicity and should be avoided, if possible. /Aminoglycosides/

What is the best way to remove kanamycin from the blood?

In the event of overdosage or toxic reaction, hemodialysis or peritoneal dialysis will aid in the removal of kanamycin from the blood. In the newborn infant, exchange transfusion may also be considered.

Does Kanamycin cause vertigo?

/SIGNS AND SYMPTOMS/ Toxic effects of kanamycin on the eighth cranial nerve can result in partially reversible or irreversible bilateral loss of hearing, loss of balance, or both. Tinnitus or vertigo may or may not be experienced. Cochlear damage is usually manifested initially by small changes in audiometric test results at the high frequencies and may not be associated with subjective hearing loss. Vestibular dysfunction is usually manifested by nystagmus, vertigo, nausea, vomiting, or acute Meniere's syndrome.

How is kanamycin given?

Kanamycin Injection may be given intramuscularly or intravenously. The patient's pretreatment body weight should be obtained for calculation of the correct dosage. The dosage of an aminoglycoside in obese patients should be based on an estimate of the lean body mass. The status of renal function should be determined by measurement of serum creatinine concentration or calculation of the endogenous creatinine clearance rate. The blood urea nitrogen (BUN) level is much less reliable for this purpose. Renal function should be reassessed frequently during therapy.

How long does it take for kanamycin to work?

At the recommended dosage level, uncomplicated infections due to kanamycin-susceptible organisms should respond to therapy in 24 to 48 hours. If definite clinical response does not occur within 3 to 5 days, therapy should be stopped and the antibiotic susceptibility pattern of the invading organism should be rechecked.

Why is kanamycin sulfate important?

Because of high concentrations of kanamycin sulfate in the urinary excretory system, patients should be well hydrated before treatment to prevent irritation of the renal tubules.

How long does kanamycin last?

The usual duration of treatment is 7 to 10 days. Total daily dose by all routes of administration should not exceed 1.5 g/day. If longer therapy is required, measurement of kanamycin peak and trough serum concentrations is particularly important as a basis for determining the adequacy and safety of the dose.

How long does it take to infuse kanamycin sulfate?

In pediatric patients the amount of diluent used should be sufficient to infuse the kanamycin sulfate over a 30- to 60-minute period.

What is the best way to remove kanamycin from the blood?

In the event of overdosage or toxic reaction, hemodialysis or peritoneal dialysis will aid in the removal of kanamycin from the blood. In the newborn infant, exchange transfusion may also be considered.

What is kanamycin used for?

INDICATIONS. Kanamycin is indicated in the short term treatment of serious infections caused by susceptible strains of the designated microorganisms below. Bacteriological studies to identify the causative organisms and to determine their susceptibility to kanamycin should be performed.

Overview

Biosynthesis

While the main product produced by Streptomyces kanamyceticus is kanamycin A, additional products are also produced, including kanamycin B, kanamycin C, kanamycin D and kanamycin X.
The kanamycin biosynthetic pathway can be divided into two parts. The first part is common to several aminoglycoside antibiotics, such as butirosin and neomycin. In it a unique aminocyclitol, 2 …

Medical uses

Side effects

Mechanism

Composition

Use in research

Antibiotic Conjugated Nanoparticle Synthesis